2-chloro-N,N,N-trimethyl-9H-purin-6-aminium chloride | 34798-88-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 2-chloro-N,N,N-trimethyl-9H-purin-6-aminium chloride
• CAS: 34798-88-4
• 化学式: C₈H₁₁ClN₅*Cl
• 分子量: 248.115
• InChiKey: ZERDXCMNZBRQHS-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -1.79
• 重原子数：
  15.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  54.46
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-chloro-N,N,N-trimethyl-9H-purin-6-aminium chloride 在 四丁基氟化铵 作用下， 以 二甲基亚砜 为溶剂， 反应 12.0h， 以90%的产率得到2-chloro-6-fluoro-9H-purine
  参考文献：
  名称：

  The New Convenient Synthesis of 6-Fluoropurine and Its 7-/9-Unsubstituted Analogues

  摘要：

  6-Fluoropurine and its 7-/9-unsubstituted analogues have good biological activity and serve as important pharmaceutical intermediates. This paper describes a new and convenient synthesis of 6-fluoropurine and its 7-/9-unsubstituted analogues, by first replacing the chlorine atoms with trimethylammonio groups through the reaction of 6-chloropurine and its 7-/9-unsubstituted analogues with trimethylamine, and then replacing the trimethylammonio groups with fluorine atoms using safe and cheap TBAF center dot 3H(2)O as fluorinating agent at room temperature. Compared with reported methods, the new synthesis has milder conditions, shorter reaction times, simpler post-processing and higher (or similar) yields.

  DOI：

  10.3987/com-12-12583
• 作为产物：
  描述：

  2,6-二氯嘌呤 、 三甲胺 以 四氢呋喃 、 水 为溶剂， 反应 12.0h， 以90%的产率得到2-chloro-N,N,N-trimethyl-9H-purin-6-aminium chloride
  参考文献：
  名称：

  The New Convenient Synthesis of 6-Fluoropurine and Its 7-/9-Unsubstituted Analogues

  摘要：

  6-Fluoropurine and its 7-/9-unsubstituted analogues have good biological activity and serve as important pharmaceutical intermediates. This paper describes a new and convenient synthesis of 6-fluoropurine and its 7-/9-unsubstituted analogues, by first replacing the chlorine atoms with trimethylammonio groups through the reaction of 6-chloropurine and its 7-/9-unsubstituted analogues with trimethylamine, and then replacing the trimethylammonio groups with fluorine atoms using safe and cheap TBAF center dot 3H(2)O as fluorinating agent at room temperature. Compared with reported methods, the new synthesis has milder conditions, shorter reaction times, simpler post-processing and higher (or similar) yields.

  DOI：

  10.3987/com-12-12583